Middleton was first settled in 1659 and was officially incorporated in 1728. Prior to 1728 it was considered a part of Salem, and contains territory previously within the limits of Andover, Boxford, and Topsfield. The name Middleton is derived from its location midway between the important early settlements of Salem and Andover. It was first settled by Bray Wilkins, who came from Salem with a large family, having purchased six hundred acres from Governor Bellingham. The town grew as a farming community, mostly due to its location on the Ipswich River, with homesteads of hundreds of acres. However, during the 18th century Middleton also contained a vital ironworks industry, located in the area of what is now Mill and Liberty streets. This enterprise originally involved Thomas Flint, Sr. and his son, Thomas Flint Jr, of Salem, John How of Boxford, and Thomas Cave Jr. of Topsfield and was carried on for approximately seventy years.

In the late 18th and to the mid-19th centuries Middleton was a vacation town to those who lived in areas such as Lawrence and Lowell. It is home to one of the oldest trees in Massachusetts, being approximately 400 years old, and which is located at 39 Peabody Street. The oldest still standing house is the Wilkins house, which was built in 1693, and served as a tavern on the main road between Salem and Lawrence.

Middleton is one of the fastest growing towns in the Commonwealth, and the fastest on the North Shore. When locally grouped it is grouped with Salem, Danvers, and Beverly, but also occasionally Topsfield and Boxford, as these three towns are a tri-town. These three towns share Masconomet Regional High School (named after Chief Masconomet, sagamore of the Agawam tribe, which lived in Essex County at the time of English colonization) which serves grades 9-12, while its Middle School serves grades 7 and 8.

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